GB1463442A - - Google Patents

Info

Publication number
GB1463442A
GB1463442A GB2283375A GB2283375A GB1463442A GB 1463442 A GB1463442 A GB 1463442A GB 2283375 A GB2283375 A GB 2283375A GB 2283375 A GB2283375 A GB 2283375A GB 1463442 A GB1463442 A GB 1463442A
Authority
GB
United Kingdom
Prior art keywords
sch
methyl
trifluoromethylcyclohexyl
triazin
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2283375A
Inventor
Hermanus Leendert Ploeg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1463442A publication Critical patent/GB1463442A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/38—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1463442 1 - Methyl - 3 - (trifluoromethylcyclohexyl) - s - triazin - 2 - one derivatives E I DU PONT DE NEMOURS & CO 23 May 1975 [24 June 1974] 22833/75 Heading C2C 1 - Methyl - 3 - (trifluoromethylcyclohexyl)- s - triazin - 2 - one derivatives of general formula where R is R 1 is -OCH 3 , -SCH 3 , -NHCH 3 or -N(CH 3 ) 2 and X is O or S, are prepared by cyclizing a compound of general formula with M 1 OR 3 , where R 2 is C 1-3 alkyl, R 3 is H or C 1-4 alkyl and M 1 is alkali metal and thereafter methylating the resulting product. Compounds where R 1 is other than -SCH 3 are obtained by reacting a compound of general formula with R 1 M 2 , where R 1 is not -SCH 3 and M 2 is H when R 1 is -NHCH 3 or -N(CH 3 ) 2 and is H or alkali metal when R 1 is -OCH 3 . Compounds where X is S are prepared by heating the corresponding compound where X is O with P 2 S 6 . Amongst numerous examples the compounds 1 - methyl - 3 - (3 - trifluoromethylcyclohexyl) - 6 - dimethylamino - s - triazin- 2,4(1H,3H) - dione and 1 - methyl - 3 - [3,5- bis - (trifluoromethyl) - cyclohexyl] - 6 - methoxy - s - triazin - 2 - one - 4 - thione are prepared. 2-, 3-, 4-, or 3,5-Bis-trifluoromethylcyclohexylamines are obtained by catalytic reduction of the appropriate aminobenzotrifluoride. 2-, 3-, 4- or 3,5-Bis-trifluoromethylcyclohexyl isocyanates are produced by reacting the above amines with phosgene. CH 3 OCONHC(SCH 3 )=NH is prepared by reacting 2-methyl-2-isothiourea sulphate with methyl chloroformate. RNHCON = C(SCH 3 )NHCOOCH 3 , where R is 2-, 3-, 4- or 3,5-bis-trifluoromethylcyclohexyl, are obtained from the above isothiourea product and above cyclohexyl isocyanates. 3 - [2-, 3-, 4- or 3,5 - Bis - trjfluoromethylcyclohexyl] - 6 - methylthio - triazin - 2,4 - diones are prepared by cyclizing the RNHCON= C(SCH 3 )NHCOOCH 3 compounds with sodium methoxide. Herbicidal compositions comprise a compound of Formula I as active ingredient together with a surfactant and/or a solid or liquid diluent.
GB2283375A 1974-06-24 1975-05-23 Expired GB1463442A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/482,792 US3933815A (en) 1974-06-24 1974-06-24 Trifluoromethyl triazines

Publications (1)

Publication Number Publication Date
GB1463442A true GB1463442A (en) 1977-02-02

Family

ID=23917477

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2283375A Expired GB1463442A (en) 1974-06-24 1975-05-23

Country Status (9)

Country Link
US (1) US3933815A (en)
JP (1) JPS5115631A (en)
AU (1) AU498259B2 (en)
BR (1) BR7503942A (en)
CA (1) CA1032942A (en)
DE (1) DE2528162A1 (en)
FR (1) FR2276303A1 (en)
GB (1) GB1463442A (en)
ZA (1) ZA753996B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2254200C2 (en) * 1972-11-06 1982-04-22 Bayer Ag, 5090 Leverkusen Tetrahydro-1,3,5-triazine-2,6-diones, process for their preparation and their use as herbicides
US4035365A (en) * 1973-11-01 1977-07-12 Imperial Chemical Industries Limited Triazinediones
US4082536A (en) * 1973-11-01 1978-04-04 Imperial Chemical Industries Limited Heterocyclic compounds and their use as pesticides
US4053299A (en) * 1975-10-10 1977-10-11 E. I. Du Pont De Nemours And Company Novel thiotriazinediones and their use as herbicides
DE2630562C2 (en) * 1976-07-07 1984-01-12 Bayer Ag, 5090 Leverkusen Process for the catalytic hydrogenation of perfluoroalkyl-substituted anilines
US4174445A (en) * 1976-10-23 1979-11-13 Bayer Aktiengesellschaft Preparation of arthropodicidally active substituted triazine-2,4-diones
DE2848670A1 (en) * 1978-11-09 1980-05-22 Bayer Ag 6- ANGULAR CLAMP ON 2-HYDROXY-4- SMALLER THAN 1,2,3-TRIAZOLYL- (2) LARGER THAN -PHENYL ANGLE CLAMP FOR -2,4- DIOXO-1,3,5-TRIMETHYL-HEXAHYDRO-S- TRIAZINE AND THEIR MANUFACTURE AND USE AS INTERMEDIATE PRODUCTS FOR THE MANUFACTURE OF OPTICAL BRIGHTENERS
JPS5843204B2 (en) * 1980-11-17 1983-09-26 株式会社 東亜機械製作所 Drill press
JPS60238207A (en) * 1984-05-07 1985-11-27 Yunipooto Trading Kk Step back mechanism

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3505057A (en) * 1962-03-22 1970-04-07 Du Pont Method for the control of plants
DE1567209A1 (en) 1964-12-14 1970-04-23 United States Borax Chem Herbicides
US3855219A (en) * 1972-07-03 1974-12-17 Du Pont 1,3,5-triazinediones
JPS5245139B2 (en) * 1973-12-14 1977-11-14

Also Published As

Publication number Publication date
JPS5115631A (en) 1976-02-07
AU8234775A (en) 1977-01-06
DE2528162A1 (en) 1976-01-15
BR7503942A (en) 1976-07-06
ZA753996B (en) 1976-05-26
US3933815A (en) 1976-01-20
AU498259B2 (en) 1979-02-22
CA1032942A (en) 1978-06-13
FR2276303A1 (en) 1976-01-23
FR2276303B1 (en) 1979-04-13

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee